(tap on any row to expand for more details)
Here's a sample itinerary for a drive from Chicago to Tallahassee. If you're planning a road trip to Tallahassee, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Chicago and Tallahassee. Camping along the way? View RV campgrounds between Chicago and Tallahassee. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
9:00 am start in Chicago
drive for about 2 hours
11:14 am eat at Triple XXX Family Restaurant
stay for about 1 hour
and leave at 12:14 pm
drive for about 1.5 hours
1:35 pm Indianapolis
stay for about 1 hour
and leave at 2:35 pm
drive for about 2 hours
4:26 pm Louisville
stay for about 1 hour
and leave at 5:26 pm
drive for about 2.5 hours
8:03 pm Nashville
stay overnight at Gaylord Opryland Resort
leave the next day around 9:00 am
day 1 driving ≈ 8 hours
find more stops
9:00 am leave from Gaylord Opryland Resort
drive for about 3 hours
11:59 am Birmingham (Alabama)
stay for about 1 hour
and leave at 12:59 pm
drive for about 1.5 hours
2:28 pm Montgomery
stay for about 1 hour
and leave at 3:28 pm
drive for about 3.5 hours
7:10 pm arrive in Tallahassee
day 2 driving ≈ 8 hours
find more stops
Triple XXX Family Restaurant
Indianapolis (34 answers)
Indianapolis Museum of Art (4 mentions)
Indianapolis Zoo (2 mentions)
questions about Indianapolis:
What is your favorite restaurant in Indianapolis?
Awesome food trucks?
Best free things to do in Indianapolis?
Your Favorite Holiday Events in Indianapolis
Louisville (43 answers)
Louisville Slugger Museum & Factory (3 mentions)
Churchill Downs (2 mentions)
Muhammad Ali Center (2 mentions)
Fourth Street Live! (2 mentions)
Louisville Slugger Field (2 mentions)
restaurants around Louisville:
Seviche, A Latin Restaurant
Basa Restaurant
Milkwood Restaurant
Jeff Ruby's Louisville
Hyatt Regency Louisville
questions about Louisville:
What is your favorite restaurant in Louisville?
Any cool things to do/places to eat in Louisville?
What's the best neighborhood in Louisville for a first time visitor?
Hotels to stay at during the Kentucky Derby?
Has anyone been to Butchertown Market?
Nashville (163 answers)
Grand Ole Opry (8 mentions)
Country Music Hall of Fame (6 mentions)
Ryman Auditorium (6 mentions)
Centennial Park (6 mentions)
The Parthenon (5 mentions)
restaurants around Nashville:
Bluebird Cafe
Opryland Hotel
Pancake Pantry
Hattie B's Hot Chicken - 19th Ave
Peg Leg Porker BBQ
hotels around Nashville:
Gaylord Opryland Resort
The Hermitage Hotel
Omni Nashville Hotel
questions about Nashville:
Nearby small towns or outdoor areas?
Top of the line hotels in Nashville?
What are some must sees in Nashville during the weekend
What's the best neighborhood in Nashville for a first time visitor?
Best Location to Stay
Birmingham (Alabama) (38 answers)
questions about Birmingham (Alabama):
Entertainment for a large group of customers in Birmingham?
locate a good breakfast or coffee shop on the west side of Birmingham
Montgomery (12 answers)
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
For example, here are some questions people have asked about Tallahassee. Click on any question to see answers from the community!
Katie from Los Angeles asked:
Best free things to do in Tallahassee? (5 answers)
Click the button below to explore more questions and answers related to Tallahassee.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Want to plan the trip back? Get the reverse directions for a Tallahassee to Chicago drive, or go to the main page to plan a new road trip.
You can also compare the travel time if you're flying or driving by calculating the distance from Chicago to Tallahassee. Or get a full Chicago to Tallahassee flight plan.
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Chicago well, please help your fellow travelers and answer their questions about Chicago!
